Winchester, KY Single family properties for sale

Spacious Investment Property in Winchester

$259,900

2,683 SF

Spacious Investment Property in Winchester

217 S Highland St, Winchester, KY 40391

Updated investment property with large living spaces and endless possibilities.

Fresh updates throughout the home.
Large living spaces.
Four bedrooms.
Two bathrooms.
Natural Gas heating.

Updated: Dec 10, 2025

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Renovated Mixed-Use Building, Winchester, KY

$299,000

3,132 SF

Renovated Mixed-Use Building, Winchester, KY

27-29 S Main St, Winchester, KY 40391

Renovated mixed-use building with storefront, apartment, and parking.

Prime Location: Directly across from the Court House on Main Street.
Live/Work Opportunity: Perfect building to live upstairs and operate your business downstairs.
Renovated Downstairs: Completely renovated storefront with new HVAC, exposed brick, and new flooring.
Partially Renovated Upstairs: Demo complete, new back deck, walls up, plaster work completed, and new back windows installed.
Opportunity Zone: Located in an Opportunity Zone.

Updated: Jan 5

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$525,000

5,094 SF

Mixed-Use Property in Winchester, KY

Versatile property with commercial space and residential income potential.

808 Bypass Rd, Winchester, KY 40391

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Based on your search, we've compiled 7 Potential Opportunities for your consideration. Besides 3 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities

Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

$514,900

3,016 SF

Luxury Townhome Near Downtown Lexington

Immaculate, updated townhome with gated park access and premium features.

104 Tradition Cir, Lexington, KY 40509

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$375,000

2,731 SF

Courtyard View Townhome Auction

Townhome with courtyard view, open floor plan, and two-car garage.

960 Village Green Ave, Lexington, KY 40509

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Frankfort Multifamily Investment Opportunity

Pending

$325,000

Frankfort Multifamily Investment Opportunity

Four properties, six units, ideal for rental portfolio expansion.

814 Holmes St, Frankfort, KY 40601

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$210,000

1,568 SF

Charming Home on 1.9 Acres

Spacious 3-bedroom home on 1.9 acres in a serene setting.

7885 Harp Pike, Frankfort, KY 40601

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Winchester, KY Single Family Properties Investment Opportunities Market Analysis

Explore 3 single family properties for sale in Winchester, KY, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 30,492 square feet of properties for sale, with an estimated market value of $1,083,900.

Sale prices for single family properties in Winchester, KY start at $259,900, averaging $361,300, and reaching up to $525,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Winchester, KY Single Family Properties for Sale

Spacious Investment Property in Winchester

Updated investment property with large living spaces and endless possibilities.